Most industrial countries have experienced a transformation of land use: from decreasing to expanding forest areas, the so-called forest transition. Outside closed forests, European rural landscapes exhibit a diversity of tree-based agricultural systems, but the question of whether this forest transition has also affected ‘trees outside forests’ has rarely been studied. The aim of this study is to analyze the spatial-temporal dynamics of farm trees and woodlands in an agricultural landscape in Eastern Germany from 1964 to 2008, based on aerial photographs and digital orthophotos. Taking a landscape ecological perspective, we quantify farm tree dynamics, disentangle processes of gain and loss in the socialist and post-socialist periods of Eastern Germany, and assess differences in ecosystem services provided by farm trees. A substantial increase of overall tree cover by 24.8% was observed for the selected time period, but trajectories have been disparate across different farm tree classes. The increase in tree cover was stronger in steep valleys than on hills and plateaus, indicating a significant interdependence between topography and trajectories of change. Patch numbers of farm trees did not increase, which suggests that the expansion of tree cover is mostly due to a spatial expansion of previously existing tree patches. Overall net gains in tree cover were rather similar during the socialist and post-socialist eras. The general increase in tree cover was accompanied by increases in agriculture-related ecosystem service provision, but the increase in pollination and pest control services was much lower than that in water purification services. These findings present the first empirical evidence from an industrialized country that there is also an ongoing ‘forest transition’ outside closed forests. Potential, partially counteracting drivers of change during the socialist and post-socialist periods have mainly been related to farm policies and the environmental consciousness of land users and society as a whole.